Corrigendum to “Novel diamino imidazole and pyrrole-containing polyamides: Synthesis and DNA binding studies of mono- and diamino-phenyl-ImPy*Im polyamides designed to target 5′-ACGCGT-3′” [Bioorg. Med. Chem. 20 (2012) 693–701]

Authors

Vijay Satam, Hope CollegeFollow
Balaji Babu, Hope College
Sameer Chavda, Hope College
Mia Savagian, Hope CollegeFollow
Robert Sjoholm, Hope CollegeFollow
Samuel Tzou, Hope CollegeFollow
Joseph Ramos, Georgia State University
Yang Liu, Georgia State University
Konstantinos Kiakos, UCL Cancer Institute, UK
Shicai Lin, UCL Cancer Institute, UK
W David Wilson, Georgia State University
John A. Hartley, UCL Cancer Institute, UK
Moses Lee, Hope CollegeFollow

Document Type

Article

Publication Date

8-1-2012

Publication Source

Bioorganic & Medicinal Chemistry

Volume Number

20

Issue Number

15

First Page

4881

Last Page

4881

Publisher

Elsevier

ISSN

0968-0896

Comments

The name of Joseph Ramos was inadvertently omitted from the author line in the original article.

Refers to:

Novel diamino imidazole and pyrrole-containing polyamides: Synthesis and DNA binding studies of mono- and diamino-phenyl-ImPy*Im polyamides designed to target 5′-ACGCGT-3′ Bioorganic & MedicinalChemistry, Volume 20, Issue 2, 15 January 2012, Pages 693-701

Abstract

Pyrrole- and imidazole-containing polyamides are widely investigated as DNA sequence selective binding agents that have potential use as gene control agents. The key challenges that must be overcome to realize this goal is the development of polyamides with low molar mass so the molecules can readily diffuse into cells and concentrate in the nucleus. In addition, the molecules must have appreciable water solubility, bind DNA sequence specifically, and with high affinity. It is on this basis that the orthogonally positioned diamino/dicationic polyamide Ph-ImPy*Im 5 was designed to target the sequence 5′-ACGCGT-3′. Py* denotes the pyrrole unit that contains a N-substituted aminopropyl pendant group. The DNA binding properties of diamino polyamide 5 were determined using a number of techniques including CD, ΔT_M, DNase I footprinting, SPR and ITC studies. The effects of the second amino moiety in Py* on DNA binding affinity over its monoamino counterpart Ph-ImPyIm 3 were assessed by conducting DNA binding studies of 3 in parallel with 5. The results confirmed the minor groove binding and selectivity of both polyamides for the cognate sequence 5′-ACGCGT-3′. The diamino/dicationic polyamide 5 showed enhanced binding affinity and higher solubility in aqueous media over its monoamino/monocationic counterpart Ph-ImPyIm 3. The binding constant of 5, determined from SPR studies, was found to be 1.5 × 10⁷ M⁻¹, which is ∼3 times higher than that for its monoamino analog 3 (4.8 × 10⁶ M⁻¹). The affinity of 5 is now approaching that of the parent compound f-ImPyIm 1 and its diamino equivalent 4. The advantages of the design of diamino polyamide 5over 1 and 4 are its sequence specificity and the ease of synthesis compared to the N-terminus pyrrole analog 2.

Keywords

Polyamides; Diamino; Dicationic; Gene control; ACGCGT; MCB; Mlu1; Cell-cycle box

Recommended Citation

Satam, Vijay, Balaji Babu, Sameer Chavda, Mia Savagian, Robert Sjoholm, Samuel Tzou, Joseph Ramos, Yang Liu, Konstantinos Kiakos, Shicai Lin, W. David Wilson, John A. Hartley and Moses Lee. "Corrigendum to “Novel Diamino Imidazole and Pyrrole-Containing Polyamides: Synthesis and Dna Binding Studies of Mono- and Diamino-Phenyl-Impy*Im Polyamides Designed to Target 5′-Acgcgt-3′” [Bioorg. Med. Chem. 20 (2012) 693–701]." Bioorganic & Medicinal Chemistry 20, no. 15.00 (2012): 4881-4881.